


Take Me Home Tonight

by eric_idle_rules



Category: Teen Wolf (TV)
Genre: Alternate Universe, Barebacking, College Student Stiles, First Time, Human Derek Hale, Karaoke, M/M, Sterekaraoke
Language: English
Status: Completed
Published: 2013-08-07
Updated: 2013-08-07
Packaged: 2017-12-22 16:27:52
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,015
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/915434
Author URL: https://archiveofourown.org/users/eric_idle_rules/pseuds/eric_idle_rules
Summary: <blockquote class="userstuff">
              <p>Friday night is Stiles’ favorite night of the week.  It's his date night with a microphone at his favorite karaoke bar.  One Friday night, he sees a very attractive broody looking man in the back of the bar and devises a strategy to use his amazing karaoke skills to catch that man's attention.</p>
            </blockquote>





	Take Me Home Tonight

**Author's Note:**

> All credit to the term "Sterekaraoke" goes to homo_pink. I now like to say it aloud. Randomly.

Friday night has become Stiles’ favorite night of the week. It has become his own personal date night, and not just with his right hand. It isn’t like it’s with anyone else, either, but who’s counting? 

His Friday nights used to consist of copious amounts of pizza, Mountain Dew (which is a bitch on his ADHD) and video games with his best friend Scott. Then, during second semester of their sophomore year of college, Scott met Allison. After that, Stiles’ Friday nights became “could I get a rain check?” nights. He’s happy for Scott, he really is, but Friday nights just aren’t the same without him. 

However, because of Scott’s ditching him for Allison, he’s able to make the greatest discovery of his life: karaoke bars. Specifically one karaoke bar, Magic Mics, that allows minors on Friday nights. So, that’s where he begins going Friday nights. At first, he just observes, sipping on a Coke because the last thing he needs is to be discovered with a fake ID and for someone to inform his father.

Then, one night, during a particularly long, drawn out rendition of American Pie, he decides it’s high time that he got up there himself. He puts in his request and before he knows it, he’s up on stage, mic in hand as he watches the monitor. When the lyrics show up and the music starts, he just begins belting out, _“I don’t know, I don’t know, I don’t know where I’m gonna go when the volcano blow!”_ He’s so far off key, it isn’t even funny, but it’s karaoke, _everyone_ is off key. People don’t actually go to karaoke bars to find the next Freddie Mercury, they go for pure entertainment. And Stiles is, if anything, entertaining. By the end of his performance, he actually has a few people singing along with him.

He and his Jimmy Buffett songs become a regular Friday night feature all through the remainder of his sophomore year and then into his junior year.

The night of his twenty-first birthday, which happens to fall on a Friday, still include a trip to his favorite karaoke bar, only he manages to drag Scott and Allison along with him, since it’s his birthday and all he wants is for them to buy him some drinks and listen to him perform some Jimmy Buffett. That night he goes with “Why Don’t We Get Drunk and Screw.” Which he ends up doing. The getting drunk part, anyway, not the screwing. Unless his hand, sheets and mattress count… he doesn’t think they do.

It’s the only time Scott and Allison accompany him to the bar. He doesn’t mind it, though. He likes his alone time at Magic Mics and the people there like him. Not any “hey, you were great out there, let’s go have sex in the bathroom,” kind of like, but that “hey, you really know how to put on a show, let me buy you beer” kind of like. But he can never complain about a free beer, so he takes it where he can get it.

~~~

The first week back from winter break of junior year concludes with a trip to the bar. Scott’s and Stiles’ apartment isn’t too far of a walk, which was a pleasant coincidence when they had found this place while looking for rentals. 

He heads inside, greeted by the bouncer, who knows him by name at this point (and still cards him, anyway). “Hey there, Stiles.”

“Hey, Jimmy. Good crowd tonight?” Stiles asks, putting his ID back into his wallet. 

“I’m sure you’ll get ‘em goin’ if they’re not.” He has long since learned to tune out all the tone deaf singing that spilled out of that bar.

Stiles smiles at him and continues heading inside. “Hey, Sheila,” he then greets the bartender, who also knows him by name.

“Stiles! Must be Friday,” she teases. “What can I get you tonight?”

“What do you feel like making me tonight?” he asks.

She loved trying out various new mixes on Stiles, since he was very openly honest, maybe sometimes a little too honest. “You feel like having some tequila tonight?”

“Tequila’s always good.”

She whips him up a frozen mixed berry margarita and slides it over to him when she’s done. “Well?”

“Holy shit, what is this? I can’t even taste tequila in this, are you sure you put it in, Sheila you are a miracle worker,” he says all in one run on sentence. He has a second one as soon as the first one’s finished.

And there is most definitely alcohol in it.

He puts in his request as soon as he finishes up the last sips of drink number two. He thinks it’s a highly appropriate song for the occasion. 

“Help me welcome to the stage, Stiles!” the DJ announces once his song is ready to go. Stiles heads up on the stage, the tequila starting to get to him, but he enjoys his drunken karaoke. The first few familiar notes of the song play before some lyrics come up on the screen and he begins singing, _“Nibblin’ on sponge cake, watchin’ the sun bake.”_ When he gets to the chorus, he sings it with enthusiasm. _“Wastin’ away again in Margaritaville! Searchin’ for my lost shaker of salt! Some people claim that there’s a woman to blame, but I know, it’s nobody’s fault!”_

He continues singing, eyes always skimming the crowd, making eye contact with fellow patrons here and there. And that’s when he sees the brooding man by the back wall. He stumbles briefly with the lyrics, but gets right back on track soon enough. But after seeing the brooding man by the back wall, he can’t take his eyes off of him. Doesn’t _want_ to take his eyes off of him, either. The guy doesn’t even notice him, but Stiles is used to gawking from afar, so it’s really just another day in the life. 

The song wraps up and the guy does actually look up, but it’s because a woman has started talking to him. After leaving the stage, Stiles heads right back over to the DJ booth, only this time he actually flips through the books looking for songs other than Jimmy Buffett. He has about thirty slips filled out when he asks, “Do you have “Jizz In My Pants”?” 

The DJ stares at him for a moment, then answers with a slow, drawn out, “No.”

“Dammit,” Stiles mutters under his breath. “Ok, these are good enough.” 

He drops the pile of tickets off with the DJ, who says to him, “We won’t have time for all these. I thought you did one song a night.”

“Change of plans,” Stiles answers as he picks through to find his five best options. “Is this better?” he asks, having dumped a majority of his slips onto the floor.

Rolling his eyes, the DJ looks them over and says, “Yeah. I’ll scatter your songs so that some other people actually have a chance, too.” He then reads all the song names a little closer and asks, “Are you here on a date?”

“I wish,” he says before heading off to the bar for another one of those magical margaritas.

It’s a few minutes, one rendition of Sweet Caroline and Proud Mary later, and the DJ is announcing Stiles back to the stage. Sheila offers to watch his drink for him and sends him off to perform. He takes the mic in his hand and scopes out broody man and still seems him with that woman, but that doesn’t deter him from putting a show on for him. Nothing ever comes from his flirtations, anyway.

He begins to sing when the lyrics start. He’s watching broody man the whole time, and knows that he’s not really paying attention. Then the chorus comes up and this is when he really hits his stride. _“You don't have to be rich to be my girl; you don't have to be cool to rule my world; ain't no particular sign I'm more compatible with; I just want your extra time and your… kiss.”_ He makes kissing sounds into the mic, possibly getting a little spit on it, but it’s all in the name of performance.

Prince wraps up and he leaves the stage to go back to the bar where Sheila hands him his drink. “What was that about?” she asks, knowing that Stiles is only ever good for one song a night.

Sighing, Stiles finds the man standing in the back of the room and says, “Him.”

Sheila raises her eyebrow as she looks and nods in approval. “Did he see you?”

“Not at all,” he answers. “But I have four songs left, so…”

“I’m impressed. I wish you all the best, Stiles.” She’s heard all about his crush on Lydia Martin back in high school and about the various guys Stiles had the hots for the past few years, but she’s never seen him actively try and pursue someone. He would be a great catch for someone, it’s just a matter of the right person coming along.

“Thanks.” He takes a long drink through his straw and keeps his eyes in broody man’s direction. That woman is still with him and they’re talking, but all night he’s never actually made a move to touch her, or her him. He considers that a plus for him.

It’s a few minutes later when he’s, once again, called to the stage. The screen tells him to yell, “I want _you_ to want _me_!” So, he does. He doesn’t get quite the reaction Cheap Trick got at Budokan, but it does get people’s attention. He starts to sing, never taking his eyes off brooding man. 

During the performance, Laura Hale starts to notice some things. Like the fact that, during the last two times the kid performed, he never seemed to look away from her brother. Her brother, who is currently sitting at a table, nursing a whiskey sour and not at all looking at the cute kid up on stage making googly eyes at him. “Holy shit,” she mutters. “Derek,” she says to him, getting him to look up at her. 

“What?”

“I think he wants you to want him.”

“What?” he repeats. 

She glances to the stage, and his eyes follow her line of sight, where some kid is currently singing, _“Didn't I, didn't I, didn't I see you cryin'?”_

“I don’t know what you’re talking about,” he says before turning his attention back to his drink.

“Derek! He’s practically serenading you with Cheap Trick! And, oh my _god_ , he sang Prince before didn’t he?! _Derek_! He wants you to want him _and_ he wants your kiss.”

“Shut. Up.” Derek gets up to go to the bar to get himself another drink and can feel Laura rolling her eyes at him as he walks away. It was her fault he was there at all. She accused him of not getting out enough, which was true, but he _liked_ not getting out enough. His last girlfriend ended up being a psycho bitch who turned him off of dating completely… and they dated back when Derek was in high school. 

Stiles watches him get up from his seat and walk away during his song, but he firmly believes that the show must go on and continues singing until the song finally ends. He just misses Derek at the bar.

Sheila gives Stiles hurt puppy dog eyes when he gets back. “If it were me you were after, I’d be all over you right now,” she tells him.

He smiles before he sits on the bar stool. “He’s probably straight, anyway.”

“Well, if I were a guy, I’d totally go gay for you.”

“Lies,” Stiles says, but grins at her. 

“You’ll get him with your next one,” she says. “What _are_ you doing next?” 

“You’ll just have to wait and see. Oh, and did you know they don’t have Jizz in My Pants? I think something needs to be done to rectify that situation.”

She laughs before heading off to get the orders of a few customers and Stiles stays at the bar, waiting for his name to get called again. There’s a three song stretch where Stiles impatiently waits. Finally he gets called. A guitar riff begins and he’s singing along with all the “ohs” at the start. It’s a last minute decision when he decides to substitute all the “she”s for “he”s. 

When the kid at the bar begins singing, _“He don't like it when it's cut n' dry; and don't like me makin' future plans,”_ that Laura nudges Derek again. “Derek, listen to him.”

So, Derek sighs and finally takes a good look at the kid up at the bar singing along with all the words.

_“Well, he can take me for a little ride_  
 _Just as long as he drive me home_  
 _Around the block, maybe once or twice_  
 _And then some lovin'. Wouldn't that be nice? Yeah!_

_I won't, but I want it_  
 _Oh, what a fool believes_  
 _I got him in my sight, but just outta reach. Oh-oh!_

_Here we go around, round round round_  
 _Run, run, runaround, yeah, round round round round.”_

“Holy shit,” Derek breaths out, mouth hanging open slightly. Laura was right. The kid was looking right at him and was blatantly changing all the lyrics to fit the gender of the person he was clearly pursuing via suggestive karaoke songs.

Laura beams. “You’re gonna do something about this, right?”

“Are you kidding? God, no.”

Her expression turns into one of disbelief. “Derek, this is only one of the sweetest things I’ve ever seen anyone do ever.”

“He’s drunk.”

“He’s not drunk! He’s probably just a little buzzed. But not drunk.” She glances back to the stage to see that the kid has already finished. “Damn you, Derek,” she mumbles.

Stiles has to wait at the bar for a little before Sheila is able to escape the crowd for a moment. “And?”

“I’m pretty sure he was watching me this time,” Stiles tells her. “He stopped watching after a bit to talk to that woman he’s with, but he was definitely watching.”

“You know, you could go over and talk to him.”

“And say what to him exactly? I’d probably stammer out something totally stupid and completely ruin what slim chance I have now.” He orders a tequila shot and downs it, shaking his head slightly from the burn.

“Stiles, you would have no problem getting this guy to go home with you if you actually tried.”

“I _am_ trying.”

She rolls her eyes at him. “You gonna tell me what’s coming next?” she asks.

“Let’s just say it involves the current state of my sex life.”

“What sex life?”

“Exactly.” That’s all he gives her on that matter. He’s already thinking of what he can do during his next song to _really_ get the guy’s attention. He has a few ideas. One more shot of tequila will probably do the trick. 

He does two more shots and then he’s back up on stage. At the last minute, he’s wondering if he should have done “Do Ya Think I’m Sexy” instead, but he can’t turn back now, and he only has one more chance if this one doesn’t work. 

Laura recognizes the song instantly and her jaw is on the floor. She turns to Derek, who’s in a similar state of shock. 

“ _I made it through the wilderness_  
 _Somehow I made it through_  
 _Didn't know how lost I was_  
 _Until I found you_

_I was beat incomplete_  
 _I'd been had, I was sad and blue_  
 _But you made me feel_  
 _Yeah, you made me feel_  
 _Shiny and new_

_Like a virgin_  
 _Touched for the very first time_  
 _Like a virgin_  
 _When your heart beats_  
 _Next to mine_.” 

While Stiles sings, he lets his free hand drift down his body, rubbing down his hip and leg and then back up over his crotch. The next time he gets to the chorus, he sings, _“Like a virgin, oh!”_ and spins with his hands in the air, nearly over turning, but he recovers swiftly. He does not need to fall on his ass while singing “Like a Virgin” only to further prove his virginal status.

Laura and Derek continue to stare. Laura going back and forth between Derek and the kid on stage who was introduced as Stiles, and Derek solely at Stiles. 

Stiles wraps up the song to a round of applause, which takes him by surprise, but he gives the crowd a little grin and a bow before leaving the stage. He heads back to the bar where Sheila is smirking at him. 

Derek, on the other hand, stands up and says, “We should go.”

“Go?! Are you kidding me?! We’re not going anywhere, not before you go find that kid.”

“And tell him what?” Derek asks.

“I don’t know! That you want to take him ‘round the block once or twice? That you want to make him feel like a virgin who’s been touched for the very first time?” Laura suggests. She wants him to get back out there, to start dating again. Even though he was her brother, she had to admit that he was a good looking guy and guy that good looking shouldn’t have to go nearly a decade without so much as touching another human being, just because his first love had been a psycho bitch.

“I am _not_ saying that.”

“Well, you’re not leaving,” Laura tells him.

“Why not?”

“Because.” That’s all she says before telling him she has to use the bathroom. She grabs her purse and heads to the bathroom.

When ten minutes have passed, Derek really becomes concerned. Until he finds out that she’s not in the bathroom. Nor is she at the bar… And the Camaro isn’t in the parking lot. “You’ve got to be shitting me,” he mutters. “That bitch.” He walks back into the bar and pulls out his phone, preparing to call a cab when the kid is introduced to the stage again. Now that Laura isn’t there judging every move he makes, he finds it a little easier to watch him.

When Stiles gets on stage, he takes a big breath to relax himself. This is his last shot. He does notice that the girl broody man was with is now gone and _also_ notes that broody man is looking at him far more intently. This is good. 

“ _Ohh, ohh, ohh_ ,” he begins, not once taking his eyes off the man in the back of the room.

Derek recognizes the song in an even shorter amount of time than the Madonna song. And, oh _god_ , he really is getting propositioned via karaoke. 

“ _I feel a hunger, it's a hunger_  
 _That tries to keep a man awake at night_  
 _Are you the answer? I shouldn't wonder_  
 _When I can feel you whet my appetite_  
 _With all the power you're releasing_  
 _It isn't safe to walk the city streets alone_  
 _Anticipation is running through me_  
 _Let's find the keys and turn this engine on_

_I can feel you breathe,_  
 _I can feel your heart beat faster, faster_

_Take me home tonight_  
 _I don't want to let you go 'til you see the light_  
 _Take me home tonight”_

Derek is pretty sure he’s never seen anyone’s hips move quite like Stiles’ are. Stiles is doing things to the microphone stand that would likely count as sexual assault, but he’s trying to drive his point home. He wants to go home tonight with someone, for the first time in his life, and he wants it to be that one guy he’s had his eye on the entire night. He keeps gyrating his hips, making movements that are so highly suggestive he’s certain they’re just overtly blatant at this point. 

The song comes to an end and Stiles stands up on the stage for just a moment after he moves the mic stand back to its starting point and then glances at broody man again. This is all he’s got. If it doesn’t work, well… it’s nothing new, so he’ll just go back to his everyday normal life, still a virgin, still spending his Friday nights alone at a karaoke bar…

As he reaches the bar, he sees Sheila give him a little smirk and a wink, then feels a body _very_ close to his own. He turns and sees broody man up close and personal. And, goddamn, he’s even better looking close up. How’s that even _legal_?

“Hi,” Stiles says, eyes wide. It’s the moment of truth, he’s either about to get shot down or go home with this guy… at least maybe makeout with this guy? Do _anything_ with this guy. 

“I’ve never seen someone use a mic stand so creatively,” Derek says, grimacing what he hopes is internally at the lame lack of introduction.

“That was my intention. I’m Stiles,” he says, extending his hand to the guy he’s had his eye on.

“Derek,” he replies, taking the offered hand.

“Look, I’m pretty buzzed, maybe a little bit drunk, but I meant everything I said.” Stiles doesn’t know why he continues after that, but he does because he’s socially awkward and has never been so close to potentially getting laid, or at least madeout with in his life, “I’m sorry if I scared off your date, but I—”

Derek’s brow furrows in confusion. “What date?”

“That girl you were with the _entire night_? Did you already forget her?”

“That was my _sister_ ,” he says.

“Ohhh, that makes a lot of sense. Now I really meant everything I said. Like, I’ve never meant anything more in my life.”

He doesn’t see Sheila mouthing things to Derek, like, “He’s a total catch,” and, “Just go for it.” He does see Derek’s internal struggle as he decides what he wants to do. He doesn’t know what a huge step it would be for Derek to throw caution to the wind and just say yes, because the last time he had that kind of attitude, he let the wrong person into his life. It’s kind of a big deal him approaching Stiles at all, even if he ends up saying no.

Which he doesn’t do. He gives a little nod and then says to Stiles, “Where, uh, where did you wanna go?”

“My place is just down the street.” They have to walk back to Stiles’ apartment because Derek is no longer in possession of his car and Stiles always walks to Magic Mics. “I’ve never seen you there before. I go every Friday. It’s kind of my thing. I know everyone there. I mean, if I’d seen you there before, I’d have tried this a whole lot sooner.”

“I wasn’t there by choice,” Derek informs him. “My sister told me I don’t get out enough… she dragged me there and then abandoned me before your grand finale.”

They’re soon in Stiles’ apartment, after far too much fumbling around with keys to be considered smooth and then Stiles is looking at Derek, who’s looking at him. And it’s… kind of awkward. 

Before either of them really know what’s happening, Derek steps in close, so he’s right in Stiles’ personal space. Stiles’ heart rate increases as he can feel Derek’s breath on his face. And then they’re kissing right up against the door to the apartment. Stiles is making all these little noises he hadn’t even know he was capable of making, but he’s kissing the most gorgeous man he’s ever seen and he’s already embarrassed himself so much tonight that he can’t get himself to care. 

When they pull apart for some air, Stiles suggests they move things into his bedroom. He really doesn’t want Scott to walk in on him; he’s done that to Scott and Allison and it was pretty uncomfortable for a while. Derek agrees and they head to the bedroom. When the door closes, their lips are fused together once again and this time Stiles’ hands starts going for Derek’s clothes, trying to remove them like he sees all the time in porn. It’s not as easy as they make it look.

Finally he pulls back from the kiss so he can focus on actually removing Derek’s shirt. He manages to get it stuck on Derek’s head. Dammit. Derek finishes pulling his own shirt off and then actually _smiles_. How is he smiling after that? “Could I ask you something?”

“You just did,” Stiles replies like a smartass twelve year old.

“Are you… are you really a virgin?”

Stiles can feel his face burning up. Of all the things Derek could have asked him… “Yeah,” he answers, feeling incredibly lame and annoyed, because his virginal status has probably turned the guy off of him.

When Derek starts kissing him again and pushes him down on the bed, he decides that, well, maybe it isn’t a total turnoff. He can feel Derek going for his clothes now and, god, even though his being a virgin didn’t turn the guy off, his slim, _slightly_ toned, blindingly pale and mole covered body probably will.

But then there is _tongue_ on his chest and _is he playing connect the dots_?! Because that is really hot. Derek’s tongue moves from the mole he knows he has on his right pec all the way down to his happy trail. There is tongue in his happy trail and it feels _amazing_.

Derek stands up and Stiles has a moment of panic when he thinks that he’s going to leave and he’s going to have to, once again, spend the night relieving himself with his hand. But then he hears the sound of pants hitting the floor and relief floods through him. He sits up on his elbows and takes a good look at the man in front of him. Wow, he has a huge dick. When he sees Derek actually smirking, he says, “Did I just say that out loud?”

“Yeah.”

Stiles falls back onto the bed and covers his face with his hands.

Everything is better, though, when hands are back on Stiles’ body and he can feel his own fly being undone. “Is this ok?” Derek asks before actually yanking Stiles’ pants off.

“Yes! More than ok! I’m encouraging you to keep going.”

So, Derek does as he’s encouraged to do and pulls down Stiles’ pants and boxers, too. And oh shit, he’s wearing his Wonder Woman boxers. “Comic book fan?” Derek asks with clear amusement in his voice.

“They were a gift from my best friend.” He really had no idea that he could even get this embarrassed; the universe is clearly conspiring against him. He’s quite honestly amazed that Derek hasn’t run far, far away from him.

Derek’s still grinning when he crawls back on top of Stiles and leans down to kiss him some more. Their now uncovered cocks rub together as they kiss and Stiles has found himself making those strange little noises again. But Derek is still there on top of him, kissing him like he’s never been kissed before (probably because he really hasn’t been kissed like this before) and it is _so_ good.

Well, he thinks it’s pretty much the best feeling in the world to have someone else’s dick rubbing against his, but he quickly discovers that he’s wrong, because when Derek’s hand grabs both of their dicks and starts rubbing up and down, he decides that that’s even better. 

He also realizes that he can get even further embarrassed when he comes less than a minute after Derek began touching him. “I’m sorry,” he says.

Derek doesn’t reply, just continues to stroke, and not too long after Stiles came, Derek comes himself. It’s been a really long time since he’s been in any sort of sexual situation.

“Holy shit, that was awesome,” Stiles says. 

“Do you want me to…” he glances at Stiles, who has an eyebrow raised at him. “I can leave if you want.”

“What?! No! I thought we were just getting started!” he exclaims. “Weren’t we? Did you want to leave? Because I don’t want to hold you here against your will if you really don’t want to be here. But if you’re really asking me if I want you to leave, then no. Not at all. Because there are _so_ many things I want to try. Like blowjobs. I’ve never given one. Or gotten one, actually. And sex. Definitely want to try that whole sex thing out.”

“I don’t know if we’ll have time for all of that tonight,” Derek says, amusement evident in his voice.

“Sooo,” Stiles drags out, “we’ve got time for _some_ of it?”

“If you want.”

“Yes! Yes, I want!” He thinks for a moment, then says, “The sex thing. We should do that.”

“Are you sure?”

“I’m twenty-one, still a virgin and have the hottest man _ever_ in my bedroom. Yes, I’m sure. We can always do the blowjob thing next time.” Stiles’ eyes go wide when he thinks about that a second afterwards. “I mean, if you _want_ there to be a next time. There doesn’t have to be.”

Instead of saying anything aloud, Derek grabs Stiles’ phone from where it sits on his bedside table and adds himself to his contacts.

Now Stiles’ mouth is hanging wide open, because, holy shit, the hot broody man actually put his number into his phone.

Derek grins, then starts kissing Stiles again. He can feel that Stiles is hard again as their bodies begin rubbing together. _He’s_ hard again, too, and he wants this to happen. It was the last thing he ever expected to come out of a night where he was dragged off to a karaoke bar of all things by Laura, but apparently, sometimes good things came out of karaoke bars. 

“Do you have… anything?” Stiles asks when they break apart. 

“No,” Derek answers. “It’s, uh, it’s been a long time, so…”

“What?” Stiles asks. “How long is a long time for you? A month? Two?”

“Ten years,” Derek says so quietly that Stiles is sure he’s misheard.

“Wait, wait, _wait_. Hold on. Did you just say ten _years_? Actual years?”

“Yeah.” He hates admitting to it, but Stiles already told him he was a virgin, so he figures it’s the least he can do to be honest with him.

“But you’re gorgeous,” Stiles says, shocked. “How can you not have been with anyone in ten _years_?”

“It was… a bad breakup,” he mutters.

“I say we take care of that right now. Two birds, one stone and all that, right?” He leans over and fishes out the lube he keeps on hand for his nightly dates with his own hand.

Derek nods, taking the lube from Stiles. He slides down Stiles’ body, all long, lean muscle, before nudging Stiles’ legs apart. Squirting some lube onto his hands, he slicks up his fingers and watches Stiles intently as he begins pushing a single finger inside. “Is this ok?” Derek asks.

“Believe me, you’ll know if something’s not ok,” Stiles informs him. “And this is totally ok.”

He pushes his finger in and out, enjoying all the little noises that Stiles is trying to not make. When he slips a second finger in alongside the first, he finds a little more resistance, but sees that Stiles is still enjoying the experience, so he doesn’t stop to ask this time. He believes that Stiles will tell him the second he’s not enjoying himself, and if Derek has things his way, there won’t be a single second that Stiles isn’t enjoying himself. His other hand is rubbing soothingly over Stiles’ thigh, trying to keep him relaxed.

While Derek fingers him and prepares him for what’s to come (which has Stiles thinking back to his embarrassing “I can’t believe I said that out loud” moment), he reaches downwards and lightly takes hold of his cock, beginning to stroke. 

When a third finger enters him, Stiles does tense up some. “It’s ok,” Derek says, still rubbing Stiles’ leg. 

“Easy for you to say. You don’t have three fingers up your ass.”

Derek actually chuckles and then leans forward to kiss Stiles. That helps him relax.

When their kiss breaks off and Derek pulls back, Stiles begins pleading with him. “Now, Derek. Do it now. _Please_.”

“And you’re sure you’re ok doing this without anything?” Derek asks.

“Ten years,” Stiles says, pointing to Derek, “virgin,” he goes onto say, pointing to himself. “Unless you’ve been sharing needles with someone, I think we’ll be ok.”

Derek snorts lightly and shakes his head. Stiles is really something else. He makes a mental note to thank Laura for dragging him out to the bar. Sitting back up, he slips his fingers out of Stiles before grabbing the bottle of lube again, this time squirting it directly onto his cock. He sucks in a small breath at the initial chill, but it warms up as he spreads it over himself. 

Stiles widens his legs even further, beyond ready to feel Derek inside him. When Derek lines himself up and begins pushing inside, they both let out gasps. Stiles because, holy fuck, his cock feels even bigger going in and Derek because it’s been so damn long and Stiles is so unbelievably tight. 

When he’s inside completely, his hips pressed right up against Stiles’ ass, he bends forward, bracing himself on his arm as he kisses Stiles again. It worked last time so he figures he’ll try it to see if it will relax him further. It does. But it also gets him even more worked up. “Oh my god, _move_ ,” Stiles pleads. 

Derek works his hips back and forth in a shallow, steady rhythm. He feels Stiles wrap his legs around him, which manages to pull them impossibly closer. 

“You can go faster, you know,” Stiles encourages, lips brushing over Derek’s as he speaks. 

But Derek doesn’t know if he really can go any faster, because he’s having a hard enough time controlling himself as it is. He’s not some teenaged virgin, but it’s been so long he can probably get away calling himself a born again virgin, and there’s just something about Stiles and the way he moves and moans that drives him up the wall with want and need. When Stiles’ legs seem to tighten around him, he decides to appease Stiles’ wishes and moves faster. The sounds of their bodies coming together over and over fill the room, alongside their moans and muffled curses. It’s better than any porno Stiles has ever seen, and he’s seen a lot.

Arching his body, Stiles lets out a surprised cry of pleasure into Derek’s mouth when Derek angles into him just right. It feels so good and Derek keeps hitting him right there, over and over.

It’s an embarrassingly short time after Derek finds Stiles’ prostate that they’re both coming, Derek deep within Stiles’ body and Stiles all over the both of them. Well, Stiles doesn’t find it all that embarrassing. He thinks eight minutes for his first time is rather impressive. 

Reaching between them, Derek slips his cock out of Stiles and isn’t really sure what to do from there. Stiles is practically passed out already, still lying on his back, staring right up at the ceiling. “Dude. I am so glad we tried the sex thing.”

Derek is still uncertain of what he should do.

At Derek’s silence, Stiles turns his head and looks over to where Derek is awkwardly perched on one side of the bed. “You know you can stay, right? I extend my offer from earlier.”

“Ok,” Derek says, sliding into the bed properly. He inches closer to Stiles, but not too close.

Stiles rolls his eyes and, with way more effort than it should be, rolls onto his side so he can throw an arm over Derek. “I never thought I’d get to be the big spoon in this relationship,” he mumbles against Derek’s shoulder. He hears a chuckle and smiles before falling asleep. 

The next morning, Stiles awakes to find that they switched at some point in the night and he was now being cuddled by Derek. He’s totally ok with that. He’s a versatile spoon.

“Derek?” he asks.

“Mmm,” is the hummed reply. 

“You, uh, want some breakfast, or something?” he offers. He’s really not sure what he’s supposed to do the morning after, considering he’s never been in this situation. But food is always good, right? People like food. 

“Sure.”

They get out of bed, Derek dressing in his clothes from the night before while Stiles grabs some new clothes from his dresser. Stiles leads the way to the kitchen area, with a pit stop for them both at the bathroom, then goes through the pantry in search of food. “Do you like Froot Loops?” Stiles asks. When Derek shrugs, he moves onto the next box of cereal until they finally settle on Corn Chex.

Derek is drinking the milk from his bowl when someone joins them in the kitchen. He bypasses all introduction and asks, “Holy shit, Stiles, do you even _know_ how loud you were last night?”

“That just makes up for every time I can hear you and Allison doing unspeakable things to one another,” Stiles retorts. “Also, this is Derek. Derek, this is my roommate, Scott.”

They look at one another and it’s a weird moment for everyone in the room. But, Scott gets over it because he’s glad that Stiles finally got laid and it appears to have been with someone that Stiles genuinely likes. 

Eventually, they all end up sitting on a ratty old couch that Stiles found on the side of the road, a handmade “FREE” sign on it watching Saturday morning cartoons. Stiles was in the middle, but was right up against Derek’s side. 

It’s when Scott gets up to use the bathroom that Stiles asks, “So, uh… I know you put your number into my phone and all and you are hanging out here with us, but… I mean, would you want to maybe go out sometime? With me?”

“Yeah,” Derek answers. 

“Really? That’s awesome, because I already have an idea for where we could go.”

Derek’s pretty sure he doesn’t like where this is going.

~~~

It’s Friday night and Derek agreed to meet Stiles at his apartment. Laura had given him a hell of a time over the week before and she was non stop when she learned that he was going back to Stiles’ place. She was happy that he was actually trying the dating thing again and she was dying to meet Stiles properly. Anyone that could bring a smile to her little brother’s face was alright in her book.

She’s still giving him a hard time about his date even as he closes the door to the Camaro.

When he arrives at Stiles’ apartment building, he sits there for a bit before pulling out his phone and texting that he’s here. 

Soon, Stiles is right at his window, telling him to get out. Derek now has a really bad feeling about what’s in store for him. Stiles gives him a kiss when he gets out of the car and takes his hand as they begin walking in the direction of Magic Mics. 

“What are we doing tonight?” Derek asks.

“Same thing I do every Friday.”

Stiles warms up the crowd with his riveting rendition of Cheeseburger in Paradise, then heads back down to the bar, where Sheila is attempting to engage Derek in conversation. It’s not going that well.

“So, how was I?” he asks.

“You were far more creative with your props last week,” Derek tells him.

“I was going back to my Parrot Head roots, thank you very much,” Stiles huffs.

They fall into conversation, Derek conversing slightly easier with Stiles than with Sheila, but talking to her isn’t as bad when Stiles is around to help better guide things along. Things are actually going pretty well. Until Derek hears, “Let’s welcome to the stage Stiles and Derek!”

Stiles grins. Derek scowls. “What the hell is this?”

“Your debut.”

Stiles drags Derek up onto the stage and when Derek sees the song they’re supposed to sing, he says, “No.”

“Yes. It’ll be fun. You need to loosen up, dude, stop being such a sourpuss.”

The music begins before Derek can argue any further.

Stiles grabs the mic and sings, “ _Don’t go breaking my heart_.” He holds the mic up to Derek, and… he’s silent.

Stiles moves onto his next line, “ _Honey if I get restless_ ,” and then, once again, there’s nothing from Derek. Stiles eyes Derek, trying to tell him in that single look that he’s not going to sing a duet by himself, so Derek better join him.

When Stiles sings the next line and holds the mic out to Derek, the man actually sings. Stiles smiles and, together, they pop Derek’s karaoke cherry.

_Don't go breaking my heart_  
 _You take the weight off me_  
 _Honey when you knock on my door_  
 _I gave you my key_

_Nobody knows it_  
 _When I was down_  
 _I was your clown_  
 _Nobody knows it_  
 _Right from the start_  
 _I gave you my heart_  
 _I gave you my heart_

By the next chorus, Derek’s actually kind of into it. Not as into it as Stiles, that level of into it is above and beyond, but it’s not as bad as he thought it would be. A few people applaud them when they’re finished the song. Sheila even made a special drink for Derek, on the house. While Derek drinks, Stiles begins making a mental list of every duet he can think of. It’s a toss up between Sonny and Cher’s I Got You Babe and Ike and Tina Turner’s Proud Mary as to what he wants them to do next Friday. Because duets are a thing he can do now, and he likes that a whole lot.

**Author's Note:**

> Song lyrics used include...
> 
> Volcano - Jimmy Buffett  
> Margaritaville - Jimmy Buffett  
> Kiss - Prince  
> I Want You to Want Me - Cheap Trick  
> Runaround - Van Halen  
> Like a Virgin - Madonna  
> Take Me Home Tonight - Eddie Money  
> Don't Go Breaking My Heart - Elton John and Kiki Dee


End file.
